Die Tautomerie des 4-Methyl- und 2-Brom-anthrachinon-1-carbonsäurechlorids. (4. Mitteilung über die Tautomerie der Anthrachinon-α-carbonsäurechloride)

A new method for the preparation of 2‐substituted 6‐chloro‐2,7‐dihydro‐3H‐dibenzo[de,h]cynnoline‐3,7‐diones has been developed. The compounds have been obtained in an original three‐step procedure comprising the oxidation of 1‐methyl‐9,10‐anthraquinones with periodate or permanganate/brominating reagent systems, cyclization to 6‐chloro‐2,7‐dihydro‐3H‐dibenzo[de,h]cynnoline‐3,7‐dione, and selective alkylation thereof. The selected processes were applied in the efficient scale‐up of specific 2,6‐substituted 2,7‐dihydro‐3H‐dibenz[de,h]cinnolin‐3,7‐dione derivatives, currently being investigated pre‐clinically as anticancer agents.

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A New Method for the Preparation of Intermediates for 2,6‐Substituted Anthrapyridazones

Cybulski

Sidoryk

Formela

et al. 2016

Journal of Heterocyclic Chem

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Layered Compounds. LII. Syntheses of Eleven Anthracenophanes

Iwama¹,

Toyoda²,

Yoshida³

et al. 1978

Bulletin of the Chemical Society of Japan

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A series of layered cyclophanes where an anthracene ring is stacked in different modes with the same or other π-systems has been synthesized by the Hofmann elimination method or photodesulfurization for studying the transannular π-electronic interaction. Photochemical and thermal interconversions have been observed between syn-(1,4)anthracenophane and its isomer and have been discussed with reference to the X-ray crystal data. From the electronic spectra it has been established that the transannular interaction increases with overlapping between the two faced aromatic rings and that when the overlap between the two chromophores is the same, the interaction increases relative to the dimension of the faced chromophore.

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Die Tautomerie des 4-Methyl- und 2-Brom-anthrachinon-1-carbonsäurechlorids. (4. Mitteilung über die Tautomerie der Anthrachinon-α-carbonsäurechloride)

Cited by 2 publications

References 5 publications

A New Method for the Preparation of Intermediates for 2,6‐Substituted Anthrapyridazones

A New Method for the Preparation of Intermediates for 2,6‐Substituted Anthrapyridazones

Layered Compounds. LII. Syntheses of Eleven Anthracenophanes

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